How I built a CX team no one ever quit

Outsourcing wasn’t cheaper, first hires set the culture, and BFCM is where you see if you got it right

Aug 21, 2025

Hi Team!

This week, I took a 6-hour trip to Toronto to speak at a Gorgias event on AI in ecom. Honestly, with 30 minutes to EWR and a flight a little over an hour, it might be an easier commute than heading into the NYC office. Plus, maple syrup.

Someone asked me how I think about CX hiring, how to weigh outsourcing, leaning on AI, and building an internal team. It is a question I have had to wrestle with firsthand, and the outcomes can be very different depending on the path you choose.

This week, I want to share what I have learned about hiring CX, the tradeoffs that matter, and why BFCM is often the moment where those decisions are tested.

I’ll leave the AI side for another time. I’ve got some spicy takes on CX hiring that are free and don’t require a $5,998 donation to Hormozi.

Let’s dive in.

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The Cost Myth: Run the Numbers

Back when I was running CX at Jones Road Beauty, I connected with another brand about our size. Similar kind of business, same ticket volume.

We had an internal crew of eight people, including shade-matching artists who were actively driving incremental revenue. They were trusted advisors for customers who were nervous about spending $46 on a foundation online without ever testing it.

Our NPS and CSAT were insanely high. Customers felt cared for and, just as importantly, they kept buying.

This other brand had a team of more than thirty outsourced agents. Tickets were cleared, but that was it. They weren’t driving revenue, weren’t inspiring loyalty, and their CSAT was struggling to stay above water.

When we compared costs, the spend was basically the same. The outcomes were not.

Like Ramit Sethi says about renting vs. buying a house: run the numbers. Outsourcing is not automatically cheaper. In many cases, it’s the expensive way to deliver a worse experience.

Building for Growth, Not Just Tickets

CX is building the foundation for retention and growth.

I’ve seen founders treat CX as a cost center, something to cover as cheaply as possible so they can focus on “real growth.” Then they wake up six months later with churn creeping up, negative reviews stacking, and a team of agents who don’t know the product or the customer. The “savings” evaporate, and the brand reputation takes a hit.

When to hire? Once you’re spending more than 30 minutes a day in the inbox, it’s time. That’s the point where your energy as a founder is better spent building the business, and where a dedicated CX hire can more than pay for themselves.

The First Hire

Your first CX hire should be a generalist. Early on, you may not need 40 hours of CX work each week, so look for someone who loves talking to customers but can also flex into ops, marketing, or wholesale when tickets are slow.

Culture matters even more than skills. That first hire sets the tone for the whole org. They are the person new team members will model. If they are empathetic, creative, and customer-obsessed, the team that follows will be too. If they are box-checkers, you’ll get a team that does the bare minimum.

Don’t limit yourself to candidates with DTC experience. Some of the best CX hires I’ve made came from outside the industry. Preschool teachers, hospitality pros, flight attendants.

If you can manage a classroom of 25 kids during a fire drill or calm down a plane full of people in turbulence, you can handle the inbox. Empathy and composure under pressure are worth more than years of macros.

And you want a self-starter. Someone who can build macros, design processes, and eventually onboard the next hire. Not just someone who can answer tickets.

Budget-wise, plan on $45k–65k for that first hire, depending on experience and market.

Finding and Evaluating Talent

Where to look:

Write a job description that sells your company. You are competing for talent. Make it clear why your brand is worth joining. I loved this one from Misen.
Post on LinkedIn, promote it, and ask your network to share. CX folks know other CX folks.
Leverage communities like the CX Friends Discord.
Don’t be afraid to poach. The best talent is usually working somewhere else.

How to evaluate:

Skip the scripted Q&A. Have a real conversation. Present scenarios. For example: “A customer ordered our bestseller for their wedding in two weeks. It arrived damaged. Walk me through your response.”

Ask how they recover after a draining interaction. The wrong answer is “I don’t get stressed.” Everyone gets stressed. The right answers are human: “I eat chocolate, I go for a walk, I journal.” You want empathy, not emotional detachment.

At both OLIPOP and JRB, I beat the odds on CX turnover. No one ever quit my team. People leveled up into other roles, but no one burned out and walked away. That’s not luck. It comes from supporting growth, giving autonomy, and making sure people feel appreciated.

Retention: Why People Stay

CX has one of the highest turnover rates in startups. The average tenure for a support rep is just over a year. The work is emotionally heavy, and in most orgs it comes with little recognition or career growth.

It doesn’t have to be that way.

When I led teams, I made appreciation a priority. Wins were shared across the company, customer praise was highlighted, and I made sure my team knew they were valued. Autonomy was another piece. I gave them room to solve problems, not just copy-paste macros. And I fought for growth opportunities across CX, across the business, even into roles outside the department.

If you want people to stay, you have to create a place where CX is respected. Not treated like the cost of doing business.

The BFCM Stress Test

Now let’s talk about BFCM. This is the moment of truth. The inbox can always pop off, but the volume is concentrated around a handful of issues. If you prepare in advance, you’ll see the payoff from your hiring decisions.

The big five:

Questions about the offer
Keep it simple. A single, clear discount outperforms a maze of tiers and bundles. Complexity confuses customers and clogs the inbox.
Shipping timelines
Make them obvious. Post them onsite, reinforce in post-purchase flows, and make sure macros and AI are ready to answer “when will my order arrive.” Do this in October, not November 20.
Order updates
Use self-service tools for order editing. Hold orders for 30 minutes before fulfillment to give customers a chance to fix mistakes without emailing.
Promo code issues
Test every scenario early. Codes fail, carts glitch. When it happens, good macros can resolve the issue in two minutes instead of twenty.
Returns and exchanges
Keep the process simple and visible. The worst move is hiding your return policy during BFCM. That only adds friction and damages trust.

AI and automation shine here, but only if you’ve done the prep weeks in advance. They should clear the repetitive load so your internal team can focus on high-value conversations: VIPs, complex cases, and moments where a frustrated customer can become a loyal one.

This is where hiring decisions show up. A strong internal team makes BFCM manageable. A weak one leaves you drowning.